ES2706475T3 - Nuevos derivados de bencimidazol como agentes antihistamínicos - Google Patents

Nuevos derivados de bencimidazol como agentes antihistamínicos Download PDF

Info

Publication number: ES2706475T3
Authority: ES; Spain
Prior art keywords: alkyl; aryl; optionally substituted; compound; cycloalkyl
Prior art date: 2014-12-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES15817402T

Other languages

English (en)

Spanish (es)

Inventor

Solanes Rosa Rodes

Tizne Roberto Olivera

Herrero Gonzalo Hernandez

Royo Víctor Rubio

Gomez Francisco Ledo

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Faes Farma SA

Original Assignee

Faes Farma SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2014-12-29

Filing date

2015-12-28

Publication date

2019-03-29

2015-12-28 Application filed by Faes Farma SA filed Critical Faes Farma SA

2019-03-29 Application granted granted Critical

2019-03-29 Publication of ES2706475T3 publication Critical patent/ES2706475T3/es

Status Active legal-status Critical Current

2035-12-28 Anticipated expiration legal-status Critical

Links

239000000739 antihistaminic agent Substances 0.000 title description 11
229940125715 antihistaminic agent Drugs 0.000 title description 7
229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 3
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 88
125000003118 aryl group Chemical group 0.000 claims abstract description 54
150000003839 salts Chemical class 0.000 claims abstract description 36
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 35
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
239000001257 hydrogen Substances 0.000 claims abstract description 27
239000012453 solvate Substances 0.000 claims abstract description 24
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 13
125000001475 halogen functional group Chemical group 0.000 claims abstract 5
125000000217 alkyl group Chemical group 0.000 claims description 61
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
201000010099 disease Diseases 0.000 claims description 17
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
208000035475 disorder Diseases 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 11
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 9
208000010668 atopic eczema Diseases 0.000 claims description 8
229960001340 histamine Drugs 0.000 claims description 7
230000000172 allergic effect Effects 0.000 claims description 6
230000008485 antagonism Effects 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229910052702 rhenium Inorganic materials 0.000 claims description 5
229910052703 rhodium Inorganic materials 0.000 claims description 5
206010010741 Conjunctivitis Diseases 0.000 claims description 4
208000024780 Urticaria Diseases 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
201000004624 Dermatitis Diseases 0.000 claims description 2
206010039083 rhinitis Diseases 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 abstract 1
239000011575 calcium Substances 0.000 description 42
238000005160 1H NMR spectroscopy Methods 0.000 description 20
-1 hydrocarbon chain radical Chemical class 0.000 description 16
239000000543 intermediate Substances 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 10
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239000000243 solution Substances 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
125000005843 halogen group Chemical group 0.000 description 9
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239000007787 solid Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
230000001387 anti-histamine Effects 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
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235000019198 oils Nutrition 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
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241001465754 Metazoa Species 0.000 description 5
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000002253 acid Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
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HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
HXXNTEDKEYTYPD-UHFFFAOYSA-N 2-ethoxyethyl 4-methylbenzenesulfonate Chemical compound CCOCCOS(=O)(=O)C1=CC=C(C)C=C1 HXXNTEDKEYTYPD-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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208000026935 allergic disease Diseases 0.000 description 4
150000001556 benzimidazoles Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 3
WOKHVBYJGBEWKK-UHFFFAOYSA-N 2-[4-[1-(2-ethoxyethyl)benzimidazol-2-yl]piperidin-1-yl]ethanol Chemical compound C(C)OCCN1C(=NC2=C1C=CC=C2)C1CCN(CC1)CCO WOKHVBYJGBEWKK-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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239000004480 active ingredient Substances 0.000 description 3
230000027455 binding Effects 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
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238000007796 conventional method Methods 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
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230000032050 esterification Effects 0.000 description 3
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229960003699 evans blue Drugs 0.000 description 3
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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ZEBSTOVUCYMPPO-UHFFFAOYSA-N 2-[2-[4-(1H-benzimidazol-2-yl)piperidin-1-yl]ethoxy]acetic acid Chemical compound N1C(=NC2=C1C=CC=C2)C1CCN(CC1)CCOCC(=O)O ZEBSTOVUCYMPPO-UHFFFAOYSA-N 0.000 description 2
QNJNKIQPMNBMKC-UHFFFAOYSA-N 2-[4-(3H-imidazo[4,5-c]pyridin-2-yl)piperidin-1-yl]ethanol Chemical compound N1=C(NC=2C=NC=CC=21)C1CCN(CC1)CCO QNJNKIQPMNBMKC-UHFFFAOYSA-N 0.000 description 2
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HBOGHPAOOWUTLB-UHFFFAOYSA-N 2-piperidin-4-yl-1h-benzimidazole Chemical compound C1CNCCC1C1=NC2=CC=CC=C2N1 HBOGHPAOOWUTLB-UHFFFAOYSA-N 0.000 description 2
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- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Pulmonology (AREA)
Ophthalmology & Optometry (AREA)
Dermatology (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Otolaryngology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ES15817402T 2014-12-29 2015-12-28 Nuevos derivados de bencimidazol como agentes antihistamínicos Active ES2706475T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP14382576.8A EP3040334A1 (fr)	2014-12-29	2014-12-29	Nouveaux dérivés de benzimidazole en tant qu'agents antihistaminiques
PCT/EP2015/081292 WO2016107848A1 (fr)	2014-12-29	2015-12-28	Nouveaux dérivés de benzimidazole utilisés comme antihistaminiques

Publications (1)

Publication Number	Publication Date
ES2706475T3 true ES2706475T3 (es)	2019-03-29

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ID=52302107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES15817402T Active ES2706475T3 (es)	2014-12-29	2015-12-28	Nuevos derivados de bencimidazol como agentes antihistamínicos

Country Status (17)

Country	Link
US (1)	US10106522B2 (fr)
EP (2)	EP3040334A1 (fr)
JP (1)	JP6585718B2 (fr)
KR (1)	KR20170097669A (fr)
CN (1)	CN107108575B (fr)
AU (1)	AU2015373457B2 (fr)
BR (1)	BR112017013998A2 (fr)
CA (1)	CA2970854A1 (fr)
CL (1)	CL2017001720A1 (fr)
CO (1)	CO2017005806A2 (fr)
EA (1)	EA033827B1 (fr)
ES (1)	ES2706475T3 (fr)
MX (1)	MX371102B (fr)
PE (1)	PE20171089A1 (fr)
PT (1)	PT3240783T (fr)
WO (1)	WO2016107848A1 (fr)
ZA (1)	ZA201704462B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP3040334A1 (fr)	2014-12-29	2016-07-06	Faes Farma, S.A.	Nouveaux dérivés de benzimidazole en tant qu'agents antihistaminiques
KR20200125923A (ko)	2017-10-16	2020-11-05	파에스 파마, 에스.에이.	빌라스틴 및 모메타손을 포함하는 수성 조성물
HUE054594T2 (hu)	2018-01-18	2021-09-28	Faes Farma Sa	Bilasztint, béta-ciklodextrint és legalább egy gélesítõszert tartalmazó szemészeti kompozíciók
RS63661B1 (sr)	2018-07-25	2022-11-30	Faes Farma Sa	Piridopirimidini kao inhibitori histaminskog h4-receptora
DE102019211434B3 (de)	2019-07-31	2020-11-05	Premium Aerotec Gmbh	Spantkomponente und verfahren zur herstellung einer spantkomponente, spant und rumpfstruktur für ein luftfahrzeug
PE20251070A1 (es)	2022-02-17	2025-04-10	Faes Farma Sa	Composicion de bilastina para la administracion parenteral una vez al dia

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NZ238863A (en) *	1990-07-19	1993-03-26	Janssen Pharmaceutica Nv	Substituted thiazolyl and pyridinyl derivatives
ES2048109B1 (es)	1992-07-20	1994-12-16	Espanola Prod Quimicos	Procedimiento de preparacion de nuevos derivados piperidicos del bencimidazol.
ES2124167B1 (es)	1996-06-04	1999-09-16	Espanola Prod Quimicos	Nuevos derivados del bencimidazol con actividad antihistaminica.
WO2002034719A1 (fr) *	2000-04-21	2002-05-02	Sankyo Company, Limited	Composes heterocycliques azotes satures
JP2001011050A (ja) *	1999-04-30	2001-01-16	Sankyo Co Ltd	含窒素飽和複素環化合物
ES2165274B1 (es) *	1999-06-04	2003-04-01	Almirall Prodesfarma Sa	Nuevos derivados de indolilpiperidina como agentes antihistaminicos y antialergicos.
WO2002036122A1 (fr) *	2000-10-30	2002-05-10	Sankyo Company,Limited	Medicaments preventifs ou therapeutiques contre l'hepatite et/ou l'hepatopathie
JP2002322059A (ja) *	2001-04-25	2002-11-08	Sankyo Co Ltd	炎症性腸疾患の予防又は治療剤
CN103896915A (zh) *	2014-04-01	2014-07-02	中国药科大学	苯并咪唑类衍生物、其制备方法及其在医药上的应用
EP3040334A1 (fr)	2014-12-29	2016-07-06	Faes Farma, S.A.	Nouveaux dérivés de benzimidazole en tant qu'agents antihistaminiques

2014
- 2014-12-29 EP EP14382576.8A patent/EP3040334A1/fr not_active Withdrawn
2015
- 2015-12-28 ES ES15817402T patent/ES2706475T3/es active Active
- 2015-12-28 US US15/540,905 patent/US10106522B2/en active Active
- 2015-12-28 EP EP15817402.9A patent/EP3240783B1/fr active Active
- 2015-12-28 PT PT15817402T patent/PT3240783T/pt unknown
- 2015-12-28 BR BR112017013998A patent/BR112017013998A2/pt not_active Application Discontinuation
- 2015-12-28 EA EA201791480A patent/EA033827B1/ru not_active IP Right Cessation
- 2015-12-28 KR KR1020177018064A patent/KR20170097669A/ko not_active Withdrawn
- 2015-12-28 PE PE2017001102A patent/PE20171089A1/es unknown
- 2015-12-28 CA CA2970854A patent/CA2970854A1/fr not_active Abandoned
- 2015-12-28 MX MX2017008495A patent/MX371102B/es active IP Right Grant
- 2015-12-28 AU AU2015373457A patent/AU2015373457B2/en not_active Ceased
- 2015-12-28 CN CN201580071539.9A patent/CN107108575B/zh not_active Expired - Fee Related
- 2015-12-28 WO PCT/EP2015/081292 patent/WO2016107848A1/fr not_active Ceased
- 2015-12-28 JP JP2017532061A patent/JP6585718B2/ja not_active Expired - Fee Related
2017
- 2017-06-13 CO CONC2017/0005806A patent/CO2017005806A2/es unknown
- 2017-06-28 CL CL2017001720A patent/CL2017001720A1/es unknown
- 2017-06-30 ZA ZA2017/04462A patent/ZA201704462B/en unknown

Also Published As

Publication number	Publication date
JP2018502075A (ja)	2018-01-25
ZA201704462B (en)	2019-09-25
PE20171089A1 (es)	2017-08-03
AU2015373457A1 (en)	2017-07-27
EA201791480A1 (ru)	2017-11-30
MX2017008495A (es)	2017-09-19
EP3240783A1 (fr)	2017-11-08
AU2015373457B2 (en)	2019-09-19
EA033827B1 (ru)	2019-11-29
BR112017013998A2 (pt)	2018-03-06
CN107108575B (zh)	2019-07-26
CO2017005806A2 (es)	2017-09-20
JP6585718B2 (ja)	2019-10-02
KR20170097669A (ko)	2017-08-28
EP3240783B1 (fr)	2018-11-21
US10106522B2 (en)	2018-10-23
CN107108575A (zh)	2017-08-29
MX371102B (es)	2020-01-16
CA2970854A1 (fr)	2016-07-07
US20180016251A1 (en)	2018-01-18
PT3240783T (pt)	2019-01-28
WO2016107848A1 (fr)	2016-07-07
CL2017001720A1 (es)	2018-03-16
EP3040334A1 (fr)	2016-07-06

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ES2706475T3 (es)	2019-03-29	Nuevos derivados de bencimidazol como agentes antihistamínicos
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BRPI0615634A2 (pt)	2011-05-24	novos compostos de diazaspiro
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TW200927121A (en)	2009-07-01	Bicyclic derivatives for use in the treatment of androgen receptor associated conditions
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JP2004512323A (ja)	2004-04-22	Ｃｃｒ５ケモカイン受容体活性のピロリジンモジュレーター
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